Water-soluble polynorbornene dyes having pendant chromophores

Abstract

Water soluble light harvesting multichromophores having a plurality of pendant chromophore groups are provided. Water soluble light harvesting multichromophores according to certain embodiments are polymers that include a polymeric backbone having norbornene repeat units, a pendant water solubilizing group component and a pendant chromophore component. Polymeric tandem dyes based on the subject multichromophores are also provided that further include an acceptor fluorophore linked to a norbornene repeat unit of the polymeric backbone and configured in energy-receiving proximity to at least one pendant donor chromophore group of the light harvesting multichromophore. Also provided are labelled specific binding members that include the subject polymeric tandem dyes. Methods of evaluating a sample for the presence of a target analyte and methods of labelling a target molecule in which the subject polymeric tandem dyes find use are also provided. Systems and kits for practicing the subject methods are also provided.

1 . A water-soluble polymeric multichromophore comprising:
 a polymeric backbone comprising norbornene repeat units;   a pendant water solubilizing group (WSG) component; and   a pendant chromophore component,   wherein each water solubilizing group and each chromophore group are linked to a norbornene repeat unit of the polymeric backbone.   
     
     
         2 . The polymeric multichromophore according to  claim 1 , wherein the pendant chromophore component comprises a donor chromophore. 
     
     
         3 . The polymeric multichromophore according to  claim 1 , wherein the pendant chromophore component comprises an acceptor chromophore. 
     
     
         4 . The polymeric multichromophore according to  claim 1 , wherein the pendant chromophore component comprises a donor chromophore and an acceptor chromophore. 
     
     
         5 . The polymeric multichromophore according to  claim 4 , wherein the donor chromophore and the acceptor chromophore are positioned in energy-transferring proximity to each other. 
     
     
         6 . The polymeric multichromophore according to  claim 1 , wherein the pendant chromophore component comprises a fused tricyclic aryl group. 
     
     
         7 . The polymeric multichromophore according to  claim 1 , wherein the pendant chromophore component comprises a heteroaryl group. 
     
     
         8 . The polymeric multichromophore according to  claim 1 , wherein the pendant chromophore component comprises a chromophore selected from the group consisting of boron-dipyrromethene (BODIPY), Rhodamine, perylene diimide (PDI), and Cyanine. 
     
     
         9 . The polymeric multichromophore according to  claim 1 , wherein the pendant chromophore component is linked to the norbornene repeat unit through a hydroxyl or a carboxylate functional group. 
     
     
         10 . The polymeric multichromophore according to  claim 1 , wherein the pendant water solubilizing group component comprises poly(ethylene) glycol (PEG). 
     
     
         11 . The polymeric multichromophore according to  claim 1 , wherein the polymeric backbone comprises a segment having a formula (NB-I): 
       
         
           
           
               
               
           
         
         wherein: 
         L 1 , L 2 , L 3  and L 4  are each independently a bond or a linker; 
         R 1 , R 2 , R 3  and R 4  are each independently selected from hydrogen, a water solubilizing group and a chromophore, wherein at least one of R 1 , R 2 , R 3  and R 4  is a chromophore and at least one of R 1 , R 2 , R 3  and R 4  is a water solubilizing group; 
         Y 1  and Y 2  are each independently selected from CR 5  and O; 
         R 5  is selected from hydrogen halogen, hydroxyl, cyano, nitro, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, substituted acyl, carboxyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein R 5  is optionally substituted with a water solubilizing group or a chromophore; and 
         n is an integer from 1 to 1000; and 
         m is an integer from 0 to 1000. 
       
     
     
         12 . (canceled) 
     
     
         13 . The polymeric multichromophore according to  claim 1 , wherein the polymeric backbone comprises a segment having a formula (NB-II): 
       
         
           
           
               
               
           
         
         wherein:
 G 1  is a selected from a terminal group, a polymer segment, a donor chromophore group, a linker and a linked specific binding member; 
 L 1 , L 2 , L 3  and L 4  are each independently a bond or a linker; 
 R 1 , R 2 , R 3  and R 4  are each independently selected from hydrogen, a water solubilizing group and a chromophore, wherein at least one of R 1 , R 2 , R 3  and R 4  is a chromophore and at least one of R 1 , R 2 , R 3  and R 4  is a water solubilizing group; 
 Y 1  and Y 2  are each independently selected from CR 5  and O; 
 
         R 5  is selected from hydrogen halogen, hydroxyl, cyano, nitro, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, substituted acyl, carboxyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein R 5  is optionally substituted with a water solubilizing group or a chromophore;
 n is an integer from 1 to 1000; 
 m is an integer from 0 to 1000; and 
 r is an integer from 0 to 10. 
 
       
     
     
         14 - 16 . (canceled) 
     
     
         17 . The polymeric multichromophore according to  claim 1 , wherein the polymeric backbone comprises a segment having a formula of:
 a) formula (NB-IIIA):   
       
         
           
           
               
               
           
         
         b) formula (NB-IIIB): 
       
       
         
           
           
               
               
           
         
         c) formula (NB-IIIC): 
       
       
         
           
           
               
               
           
         
       
       or
 d) formula (NB-IIID): 
 
       
         
           
           
               
               
           
         
         wherein:
 G 1  is a selected from a terminal group, a polymer segment, a donor chromophore group, a linker and a linked specific binding member; 
 L 5 , L 6  and L 7  are each independently a bond or a linker; 
 Z 1 , Z 2  and Z 3  are each independently selected from a chromophore; 
 Y 1  and Y 2  are each independently selected from CR 5  and O; 
 
         R 5  is selected from hydrogen halogen, hydroxyl, cyano, nitro, alkyl, substituted alkyl, alkoxy, substituted alkoxy, acyl, substituted acyl, carboxyl, aryl, substituted aryl, heteroaryl and substituted heteroaryl, wherein R 5  is optionally substituted with a water solubilizing group or a chromophore;
 n and m are each independently an integer from 1 to 1000; 
 r is an integer from 0 to 10; and 
 S 1 -S 3  are each independently an integer from 1 to 50. 
 
       
     
     
         18 - 21 . (canceled) 
     
     
         22 . The polymeric multichromophore according to  claim 1 , wherein the pendant chromophore component comprises BODIPY or a derivative thereof. 
     
     
         23 - 24 . (canceled) 
     
     
         25 . The polymeric multichromophore according to  claim 1 , wherein the pendant chromophore component comprises a Rhodamine or a derivative thereof. 
     
     
         26 - 27 . (canceled) 
     
     
         28 . A polymeric tandem dye comprising:
 a light harvesting chromophore comprising:   a polymeric backbone comprising norbornene repeat units;   a pendant water solubilizing (WSG) component; and   a pendant donor chromophore component,   wherein each water solubilizing group and each chromophore group are linked to a norbornene repeat unit of the polymeric backbone; and   an energy acceptor comprising a pendant acceptor fluorophore covalently bonded to the polymeric backbone in energy-receiving proximity to the donor chromophore.   
     
     
         29 . The polymeric tandem dye according to  claim 28 , wherein the pendant donor chromophore comprises a fused tricyclic aryl group or a heteroaryl group. 
     
     
         30 . The polymeric tandem dye according to  claim 28 , wherein the pendant donor chromophore is selected from the group consisting of BODIPY, Rhodamine, perylene diimide (PDI), and Cyanine. 
     
     
         31 - 51 . (canceled) 
     
     
         52 . A method comprising contacting a first norbornene monomer comprising a pendant chromophore component with a second norbornene monomer comprising a pendant water solubilizing group component to generate a polymeric backbone comprising a norbornene repeat unit, a pendant water solubilizing group (WSG) component and a pendant chromophore component. 
     
     
         53 . The method according to  claim 52 , wherein the first norbornene monomer further comprises a water solubilizing group component. 
     
     
         54 - 64 . (canceled)